EP0520320A3 - Tetrahydropyrrolo 1,2-a pyrazine-4-spiro-3'-pyrrolidine derivatives, processes for the preparation thereof and pharaceutical compositions containing the same - Google Patents

Tetrahydropyrrolo 1,2-a pyrazine-4-spiro-3'-pyrrolidine derivatives, processes for the preparation thereof and pharaceutical compositions containing the same Download PDF

Info

Publication number
EP0520320A3
EP0520320A3 EP19920110270 EP92110270A EP0520320A3 EP 0520320 A3 EP0520320 A3 EP 0520320A3 EP 19920110270 EP19920110270 EP 19920110270 EP 92110270 A EP92110270 A EP 92110270A EP 0520320 A3 EP0520320 A3 EP 0520320A3
Authority
EP
European Patent Office
Prior art keywords
tetrahydropyrrolo
pyrazine
spiro
processes
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP19920110270
Other versions
EP0520320B1 (en
EP0520320A2 (en
Inventor
Toshiyuki Negoro
Makoto Murata
Shozo Ueda
Buichi Fujitani
Yoshiyuki Ono
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Pharma Co Ltd
Original Assignee
Dainippon Pharmaceutical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dainippon Pharmaceutical Co Ltd filed Critical Dainippon Pharmaceutical Co Ltd
Priority to SG1996000934A priority Critical patent/SG55000A1/en
Publication of EP0520320A2 publication Critical patent/EP0520320A2/en
Publication of EP0520320A3 publication Critical patent/EP0520320A3/en
Application granted granted Critical
Publication of EP0520320B1 publication Critical patent/EP0520320B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/20—Spiro-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3'-pyrrolidine derivatives of the formula: <CHEM> wherein R<1> and R<2> are independently hydrogen, halogen, trifluoromethyl, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, or nitro, and R<3> is hydrogen, halogen or alkyl having 1 to 6 carbon atoms, and pharmaceutically acceptable salts thereof, processes for preparation thereof, and pharmaceutical composition containing the same. Said compounds and their salts show excellent aldose reductase inhibitory activity and are useful for the prevention and treatment of diabetic complications.
EP92110270A 1991-06-26 1992-06-17 Tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3'-pyrrolidine derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same Expired - Lifetime EP0520320B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SG1996000934A SG55000A1 (en) 1991-06-26 1992-06-17 Tetrahydropyrrolo (1,2-a) pyrazine-4-spiro-3' -pyrrolidine derivatives processes for the preparation thereof and pharmaceutical compositions containing the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP03183185 1991-06-26
JP183185/91 1991-06-26

Publications (3)

Publication Number Publication Date
EP0520320A2 EP0520320A2 (en) 1992-12-30
EP0520320A3 true EP0520320A3 (en) 1993-03-24
EP0520320B1 EP0520320B1 (en) 1997-09-10

Family

ID=16131263

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92110270A Expired - Lifetime EP0520320B1 (en) 1991-06-26 1992-06-17 Tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3'-pyrrolidine derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same

Country Status (21)

Country Link
US (1) US5258382A (en)
EP (1) EP0520320B1 (en)
JP (1) JP2516147B2 (en)
KR (1) KR100241196B1 (en)
CN (1) CN1034176C (en)
AT (1) ATE157980T1 (en)
AU (1) AU648901B2 (en)
CA (1) CA2071273C (en)
DE (1) DE69222096T2 (en)
DK (1) DK0520320T3 (en)
ES (1) ES2108717T3 (en)
FI (1) FI98066C (en)
GR (1) GR3024870T3 (en)
HK (1) HK1001728A1 (en)
HU (1) HU218214B (en)
IE (1) IE921891A1 (en)
MX (1) MX9203231A (en)
NO (1) NO300637B1 (en)
NZ (1) NZ243255A (en)
TW (1) TW202450B (en)
ZA (1) ZA924425B (en)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3195455B2 (en) * 1993-01-06 2001-08-06 ウェルファイド株式会社 Quinoline-3-acetic acid derivatives, their production and use
JP3681082B2 (en) * 1996-06-27 2005-08-10 住友ベークライト株式会社 Imido ring-containing epoxy resin and epoxy resin composition
DE69830333T2 (en) * 1997-10-20 2006-01-26 Dainippon Pharmaceutical Co., Ltd. FAST-MEDICAL DRUG COMPOSITION CONTAINING MICRONIZED AS-3201
JP2007246539A (en) * 1997-10-20 2007-09-27 Dainippon Sumitomo Pharma Co Ltd Rapidly soluble drug composition
CN1152686C (en) * 1997-10-20 2004-06-09 大日本制药株式会社 Stable drug composition
WO2001034148A1 (en) * 1999-11-11 2001-05-17 Kyorin Pharmaceutical Co., Ltd. Solid preparations for oral use
ATE319712T1 (en) 1999-12-21 2006-03-15 Mgi Gp Inc HYDANTOIN DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR USE THEREOF
JP4552189B2 (en) * 2002-11-14 2010-09-29 小野薬品工業株式会社 Treatment for spinal stenosis
US8003808B2 (en) * 2006-07-07 2011-08-23 Dainippon Sumitomo Pharma Co., Ltd. 3-hydrazino-2,5-dioxopyrrolidine-3-carboxylates, process for production of the same, and use of the same
EP2058300B1 (en) * 2006-08-31 2013-01-09 Dainippon Sumitomo Pharma Co., Ltd. Succinic acid diester derivative, process for production thereof, and use of the derivative in the production of pharmaceutical preparation
WO2008035735A1 (en) 2006-09-20 2008-03-27 Nissan Chemical Industries, Ltd. Method for producing optically active succinimide compound
CN101516843B (en) * 2006-09-27 2011-06-15 日产化学工业株式会社 Method for producing succinimide compound
US20110190497A1 (en) * 2006-09-29 2011-08-04 Daisuke Tanaka Process for production of 2,5 dioxopyrrolidine 3 carboxylate
WO2008050847A1 (en) 2006-10-25 2008-05-02 Dainippon Sumitomo Pharma Co., Ltd. Granular preparation prevented from caking
JPWO2008081860A1 (en) * 2006-12-28 2010-04-30 大日本住友製薬株式会社 Optically active succinimide derivative, production method thereof and use thereof
WO2008136527A1 (en) * 2007-05-08 2008-11-13 Dainippon Sumitomo Pharma Co., Ltd. Method for purification of optically active dioxopyrrolidine derivative
EP2164488A1 (en) * 2007-07-13 2010-03-24 Eisai R&D Management Co., Ltd. Ampa receptor antagonists and aldose reductase inhibitors for neuropathic pain
JP2011026201A (en) * 2007-10-17 2011-02-10 Mitsubishi Tanabe Pharma Corp Stereo-selective method of producing optically active pyrrolyl-succinimide derivative
JP5697998B2 (en) 2009-02-06 2015-04-08 大日本住友製薬株式会社 Process for producing optically active succinimide derivative and intermediate thereof
WO2012014953A1 (en) 2010-07-29 2012-02-02 大日本住友製薬株式会社 Process for production of optically active succinimide derivative
EP2671589A4 (en) 2011-02-02 2014-11-19 Public Univ Corp Nagoya City Univ Medicinal agent for prevention or treatment of diseases associated with intraocular neovascularization and/or intraocular vascular hyperpermeability
US10034880B2 (en) * 2014-09-11 2018-07-31 Sumitomo Dainippon Pharma Co., Ltd. Ophthalmic suspension formulation
CN106928234A (en) * 2017-02-07 2017-07-07 上海合全药业股份有限公司 （The nafoxidine of 2 benzyl 1,2,3,4 simultaneously [1,2 a] pyrazine）The synthetic method of 4 methyl alcohol

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0147805A2 (en) * 1983-12-28 1985-07-10 Kyorin Pharmaceutical Co., Ltd. Spiro-linked pyrrolidine-2,5-diones and process for their preparation
EP0173497A1 (en) * 1984-08-14 1986-03-05 Pfizer Inc. Tetracyclic spiro-hydantoin aldose reductase inhibitors
EP0365324A1 (en) * 1988-10-20 1990-04-25 American Home Products Corporation Spiro-isoquinoline-pyrrolidine tetrones and analogs thereof useful as aldose reductase inhibitors

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63132889A (en) * 1986-11-21 1988-06-04 Tanabe Seiyaku Co Ltd Quinazolinone derivative

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0147805A2 (en) * 1983-12-28 1985-07-10 Kyorin Pharmaceutical Co., Ltd. Spiro-linked pyrrolidine-2,5-diones and process for their preparation
EP0173497A1 (en) * 1984-08-14 1986-03-05 Pfizer Inc. Tetracyclic spiro-hydantoin aldose reductase inhibitors
EP0365324A1 (en) * 1988-10-20 1990-04-25 American Home Products Corporation Spiro-isoquinoline-pyrrolidine tetrones and analogs thereof useful as aldose reductase inhibitors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 82, no. 23, 9 June 1975, Columbus, Ohio, US; abstract no. 156398q, A. MORITOMO ET AL. 'Pyrrole lactame derivatives with antiprotozoa antitrichomonas blood sugar decreasing and gastric juice apoleptic activity' page 621 ; *

Also Published As

Publication number Publication date
CA2071273A1 (en) 1992-12-27
FI922848A0 (en) 1992-06-18
JPH05186472A (en) 1993-07-27
EP0520320B1 (en) 1997-09-10
FI98066C (en) 1997-04-10
NO922512L (en) 1992-12-28
AU648901B2 (en) 1994-05-05
CN1034176C (en) 1997-03-05
ZA924425B (en) 1993-03-31
ES2108717T3 (en) 1998-01-01
KR100241196B1 (en) 2000-03-02
NZ243255A (en) 1994-03-25
DE69222096D1 (en) 1997-10-16
DE69222096T2 (en) 1998-01-22
US5258382A (en) 1993-11-02
DK0520320T3 (en) 1997-10-13
IE921891A1 (en) 1992-12-30
AU1848392A (en) 1993-01-14
HU9202105D0 (en) 1992-10-28
CA2071273C (en) 2002-08-20
NO300637B1 (en) 1997-06-30
TW202450B (en) 1993-03-21
GR3024870T3 (en) 1998-01-30
KR930000519A (en) 1993-01-15
HU218214B (en) 2000-06-28
FI98066B (en) 1996-12-31
EP0520320A2 (en) 1992-12-30
MX9203231A (en) 1993-08-01
ATE157980T1 (en) 1997-09-15
FI922848A (en) 1992-12-27
HUT63424A (en) 1993-08-30
HK1001728A1 (en) 1998-07-03
CN1068825A (en) 1993-02-10
JP2516147B2 (en) 1996-07-10
NO922512D0 (en) 1992-06-25

Similar Documents

Publication Publication Date Title
GR3024870T3 (en) Tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3&#39;-pyrrolidine derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same
AU572252B2 (en) 5-methyl-4,5 dihydro-3(2h) pyridazinone derivatives
HUT77225A (en) Condensed izoxazoloxy- and -thioalkylamine derivatives, process for the preparation thereof and pharmaceutical compositions containing them
EP1035123A4 (en) Novel heterocyclic compounds
CA2029420A1 (en) Pharmaceutical compositions and methods for inhibition of maillard&#39;s reaction
TW377352B (en) Pyrido[2,3-d]pyrimidine derivatives and pharmaceutical compositions thereof
EP0433679A3 (en) Pharmaceutical compositions for inhibition of maillard&#39;s reaction
CA2042113A1 (en) Spiro-isoquinoline-pyrrolidines and analogs thereof useful as aldose reductase inhibitors
AU1507888A (en) New bicyclic compounds, processes for preparation thereof and pharmaceutical composition comprising the same
HUT49882A (en) Process for producing new spiro square brackets open chroman-4,4&#39;-imidazolidine square brackets closed derivatives and pharmaceutical compositions comprising these compounds as active ingredient
CA2042112A1 (en) N&#39;-alkyl-spiro-isoquinoline-pyrrolidine tetrones and analogs thereof useful as aldose reductase inhibitors
GR70356B (en)
AU586089B2 (en) Phosphodiesterace type 111 inhibitors having a thiadiazinone ring as part of a tricyclic structure
SG47554A1 (en) 1&#39;-amino-2-[(benzothiazolyl)methyl)]spiro [isoquinoline-4(1H),3&#39;-pyrrolidine]-1,2&#39;,3,5&#39;(2H)-tetrones and analogs thereof useful as aldose reductase inhibitors

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL PT SE

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL PT SE

17P Request for examination filed

Effective date: 19930818

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

17Q First examination report despatched

Effective date: 19960920

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: DAINIPPON PHARMACEUTICAL CO., LTD.

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL PT SE

REF Corresponds to:

Ref document number: 157980

Country of ref document: AT

Date of ref document: 19970915

Kind code of ref document: T

REG Reference to a national code

Ref country code: CH

Ref legal event code: NV

Representative=s name: BOVARD AG PATENTANWAELTE

Ref country code: CH

Ref legal event code: EP

ITF It: translation for a ep patent filed

Owner name: JACOBACCI & PERANI S.P.A.

REG Reference to a national code

Ref country code: DK

Ref legal event code: T3

REF Corresponds to:

Ref document number: 69222096

Country of ref document: DE

Date of ref document: 19971016

REG Reference to a national code

Ref country code: GR

Ref legal event code: FG4A

Free format text: 3024870

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2108717

Country of ref document: ES

Kind code of ref document: T3

ET Fr: translation filed
REG Reference to a national code

Ref country code: PT

Ref legal event code: SC4A

Free format text: AVAILABILITY OF NATIONAL TRANSLATION

Effective date: 19971205

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

REG Reference to a national code

Ref country code: CH

Ref legal event code: PFA

Owner name: DAINIPPON SUMITOMO PHARMA CO., LTD.

Free format text: DAINIPPON PHARMACEUTICAL CO., LTD.#6-8, DOSHO-MACHI 2-CHOME, CHUO-KU#OSAKA-SHI, OSAKA-FU (JP) -TRANSFER TO- DAINIPPON SUMITOMO PHARMA CO., LTD.#6-8 DOSHO-MACHI 2-CHOME CHUO-KU, OSAKA-SHI#OSAKA-FU (JP)

NLT1 Nl: modifications of names registered in virtue of documents presented to the patent office pursuant to art. 16 a, paragraph 1

Owner name: DAINIPPON SUMITOMO PHARMA CO. LTD.

REG Reference to a national code

Ref country code: PT

Ref legal event code: PD4A

Owner name: DAINIPPON SUMITOMO PHARMA CO., LTD., JP

Effective date: 20060306

REG Reference to a national code

Ref country code: FR

Ref legal event code: CD

REG Reference to a national code

Ref country code: CH

Ref legal event code: PFA

Owner name: DAINIPPON SUMITOMO PHARMA CO., LTD.

Free format text: DAINIPPON SUMITOMO PHARMA CO., LTD.#6-8 DOSHO-MACHI 2-CHOME CHUO-KU, OSAKA-SHI#OSAKA-FU (JP) -TRANSFER TO- DAINIPPON SUMITOMO PHARMA CO., LTD.#6-8 DOSHO-MACHI 2-CHOME CHUO-KU, OSAKA-SHI#OSAKA-FU (JP)

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20110613

Year of fee payment: 20

Ref country code: PT

Payment date: 20110426

Year of fee payment: 20

Ref country code: FR

Payment date: 20110513

Year of fee payment: 20

Ref country code: ES

Payment date: 20110516

Year of fee payment: 20

Ref country code: GR

Payment date: 20110509

Year of fee payment: 20

Ref country code: CH

Payment date: 20110607

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: LU

Payment date: 20110708

Year of fee payment: 20

Ref country code: BE

Payment date: 20110525

Year of fee payment: 20

Ref country code: AT

Payment date: 20110624

Year of fee payment: 20

Ref country code: GB

Payment date: 20110620

Year of fee payment: 20

Ref country code: DK

Payment date: 20110610

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20110613

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20110615

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20110702

Year of fee payment: 20

REG Reference to a national code

Ref country code: DE

Ref legal event code: R071

Ref document number: 69222096

Country of ref document: DE

REG Reference to a national code

Ref country code: DE

Ref legal event code: R071

Ref document number: 69222096

Country of ref document: DE

REG Reference to a national code

Ref country code: PT

Ref legal event code: MM4A

Free format text: MAXIMUM VALIDITY LIMIT REACHED

Effective date: 20120617

REG Reference to a national code

Ref country code: NL

Ref legal event code: V4

Effective date: 20120617

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

BE20 Be: patent expired

Owner name: *DAINIPPON SUMITOMO PHARMA CO. LTD

Effective date: 20120617

REG Reference to a national code

Ref country code: DK

Ref legal event code: EUP

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

Expiry date: 20120616

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20120619

REG Reference to a national code

Ref country code: SE

Ref legal event code: EUG

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20120616

Ref country code: PT

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20120626

REG Reference to a national code

Ref country code: GR

Ref legal event code: MA

Ref document number: 970402515

Country of ref document: GR

Effective date: 20120618

REG Reference to a national code

Ref country code: AT

Ref legal event code: MK07

Ref document number: 157980

Country of ref document: AT

Kind code of ref document: T

Effective date: 20120617

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20121122

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20120618